Potassium Carbonate → HCID 11763485, compound

HRID 864528Notes

Reaction equation

HRID 864528 reaction equation
O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.Br/[C:18](=[CH:26]\[C:27]1[C:35]2[C:30](=[CH:31][C:32]([Cl:37])=[CH:33][C:34]=2[Cl:36])[N:29]([S:38]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)(=[O:40])=[O:39])[C:28]=1[C:48]([O:50][CH2:51][CH3:52])=[O:49])/[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[S:53]1[CH:57]=[CH:56][CH:55]=[C:54]1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1CCCCC1.C1CCCCC1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[S:53]1[CH:57]=[CH:56][CH:55]=[C:54]1/[C:18](=[CH:26]/[C:27]1[C:35]2[C:30](=[CH:31][C:32]([Cl:37])=[CH:33][C:34]=2[Cl:36])[N:29]([S:38]([C:41]2[CH:42]=[CH:43][C:44]([CH3:47])=[CH:45][CH:46]=2)(=[O:40])=[O:39])[C:28]=1[C:48]([O:50][CH2:51][CH3:52])=[O:49])/[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 521585Tris(furan-2-yl)phosphaneHCID 27339602-Thiopheneboronic acidHCID 11157837HCID 11157837, compound

Product 1

HCID 11763485HCID 11763485, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolventHCID 21895417Cyclohexane diethyletherSolvent

Conditions

Temperature
60 °C

Procedure

Combine tris(dibenzylideneacetone)dipalladium(0) (412 mg, 0.450 mmol) and tri-(fur-2-yl)phosphine (837 mg, 3.60 mmol) in tetrahydrofuran (60 mL). After 5 minutes, add (Z)-2-bromo-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester (1.85 g, 3.0 mmol), thiophene-2-boronic acid (1.12 g, 9.20 mmol), and powdered potassium carbonate (1.27 g, 9.2 mmol). Heat to 60° C. After 8 days, dilute the reaction mixture with cyclohexane (120 mL) and chromatograph on silica gel eluting with 3/1 cyclohexane/ether to give the title compound. 1H NMR (CDCl3) δ 7.97 (d, 1H, J=1.7 Hz), 7.80 (d, 2H, J=8.5 Hz), 7.64 (s, 1H), 7.27 (d, 2H, J=8.5 Hz), 7.23 (d, 1H, J=1.7 Hz), 7.16 (dd, 1H, J=5.1, 1.2 Hz), 6.83 (dd, 1H, J=3.7, 1.2 Hz), 6.75 (dd, 1H, J=5.1, 3.7 Hz), 4.24 (q, 2H, J=7.1 Hz), 2.39 (s, 3H), 1.57 (s, 9H), 1.26 (t, 3H, J=7.1 Hz).

Workup

  1. waitAfter 8 days

Sources & evidence

ORD record
ord-383f494f9f514777a3e9351b052b9a79
Source dataset
uspto-grants-1996_10
Patent number
US05563157

Reaction notes

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